Design and synthesis of 1,3-dicapryloyl-2-acetylglycerol as molecular probe for triacylglycerol metabolism study

• Main Authors: Lei, Qiong, Lee, Wilson Liangwei, Li, Tianhu
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Biological sciences::Biochemistry
• Online Access: https://hdl.handle.net/10356/101899; http://hdl.handle.net/10220/19828
• Institution: Nanyang Technological University

The increasing number of health issues caused by obesity and lack of healthy and efficient fat substitutes require development on new fat substitute. This study proposes a new potential reduced-calorie structured triacylglycerol (TAG) of “1,3-medium-chain, 2-short-chain triglycerides (MSM)” configuration, and the fat substitution method is based on the suppression of 2-monoacylglycerol absorption into intestinal cells, which would decrease the recombination of TAG and reduce lipid absorption in the digestive tract. A molecular probe, 1,3-dicapryloyl-2-acetylglycerol, is offered for nutritionists to conduct further study on its metabolism in human body. The synthesis method for this structured TAG starts from the lipase-catalyzed esterification between glycerol and caprylic acid, yielding 1,3-dicapryloylglycerol, and is followed by direct esterification with acetic anhydride to form 1,3-dicapryloyl-2-acetylglycerol. Its structure is characterized by FTIR,1H NMR,13C NMR, and LC-ESI-MS.